Dentifrice compositions comprising sarcosides with calcium polyphosphate and hydrated aluminum oxide polishing agents



Unite States The present invention relates to dentifrice compositions comprising in combination a higher aliphatic acyl amide of an amino-carboxylic compound having the property of increasing the resistance of tooth enamel to acid attack, and a mixture of a calcium polyphosphate and hydrated aluminum oxide as a polishing material, as hereinafter described and claimed.

From US. Patent 2,689,170, it is known that dental preparations containing certain aliphatic acyl amides of amino acids as active ingredients possess unusual properties for the inhibition of dental caries. As described therein, the use of such dental preparations inhibits for a prolonged period of time the production of acid in the mouth from fermentable carbohydrates. In addition, it is indicated that these active ingredients possess also the property of reducing the solubility of tooth enamel in acid solution to varying degrees. It is stated that sodium N-palmitoyl sarcoside reduces the solubility of the tooth enamel to a substantial degree whereas the lauroyl sarcoside reduces enamel solubility slightly and the myristoyl sarcoside gives intermediate effects. Such results have been described also in the proceedings of Society for Experimental Biology and Medicine, November 1954, pages 332-634 by Volker et al.

In accordance with the present invention, it has been found that palmitoyl sarcoside or the like, and a polishing material comprising calcium polyphosphate and hydrated aluminum oxide are highly compatible in combination and exhibit superior characteristics for the protection of the teeth against tooth decay. For example,

atent it has been found in enamel solubility tests that a mixture of sodium N-palmitoyl sarcoside, calcium pyrophosphate and aluminum oxide trihydrate is markedly effective for inhibiting the solubility of tooth enamel in acid solution. Such dentifrice preparation exhibits a synergistic effect in this property since the reduction in enamel solubility is greater than the effects obtained by mixtures of the palmitoyl sarcoside with either calcium pyrophosphate or with the hydrated aluminum oxide under equivalent conditions. Furthermore, a dentrifice comprising these three essential ingredients inhibits satisfactorily for a prolonged period of time the production of acid from fermentable carbohydrates by the action of saliva. Such dentrifrice possesses desirable physical characteristics, par ticularly as a dental cream, in its stability to adverse conditions or to aging, effective cleansing power, and the like.

The dentrifrice compositions contain a substantially saturated higher aliphatic acyl amide of an aminocarboxylic acid compound which substantially increases the resistance of tooth enamel to acid attack. Laboratory tests for determination of this property are known in the art as described by Volker et al. It is preferred to employ a palmitoyl sarcoside, and particularly the sodium salt, in view of the outstanding effects obtained thereby. Other substantially saturated fatty acyl sarcosides having 14 to 18 carbons in the acyl group which exhibit a significant effect in such tests but to a much lesser degree are sodium myristoyl, n-pentadecanoyl, n-heptadecanoyl and stearoyl sarcosides.

Patented May 8, 1962 Such materials may be employed in the dentrifrice in the form of the free acid or water-soluble salts thereof such as sodium, potassium and triethanolamine salts, which are included within the term aminocarboxylic acid compound or sarcoside.

The aminocarboxylic acid compounds are employed in substantially pure or pure form. They should be as free as practicable from soap or similar higher fatty acid material which tends to substantially reduce the effect of such compounds. For example, it has been found that the presence of significant amounts of sodium palmitate tends to decrease the effectiveness of the sodium palmitoyl sarcoside for reducing enamel solubility in acid solution. In usual practice the amount of such higher fatty acid material is less than 15% by weight of the amide compound and insufiicient to substantially adversely affect it, and preferably less than 10% of said amide material.

It is an embodiment of the present invention that the palmitoyl sarcoside or the like may be admixed advantageously with the lauroyl sarcoside, particularly when these materials are employed within certain proportions. The ratio of the palmitoyl sarcoside to the lauroyl sarcoside is preferably from 5:1 to 1:1 by Weight and usually from about 3:1 to 2:1 by weight for optimum effects. The incorporation of such minor amount of the lauroyl sarcoside tends to improve the foaming characteristics of the composition and aids in the solubilization of the palmitoyl sarcoside in a dental cream. It has been found that such mixtures may exhibit superior effects in the reduction of enamel solubility in acid compared to the effect of the palmitoyl sarcoside alone at equivalent concentrations of sarcoside material. In general, where the lauroyl sarcoside is employed in an amount in excess of the palmitoyl sarcoside, it tends to reduce or partially repress the activity of the palmitoyl compound for reduction of enamel solubility.

Suitable water-insoluble calcium polyphosphate materials for use in admixture with the hydrated aluminum oxide include calcium pyrophosphate, metaphosphate and triphosphate.

obtained with its use.

Suitable examples of hydrated aluminum oxide are the forms known as alpha and beta aluminum oxide trihydrate and mixtures thereof, and precipitated aluminum hydroxide or alumina hydrate or alumina gel. It is used in the form of fine particles of any desired particle size. In practice, it is preferred to use the alpha trihydrate form of which at least about of the particles pass through on a US. standard No. 325 mesh sieve and not more than about 5% of the particles are less than 5 microns.

These ingredients should be used in suitable proportions. The palmitoyl sarcoside compound or the like is employed in a minor and effective amount. It will be used usually within the range of about 0.55%, preferably 14%, by weight of the dentifrice composition. Where it is used in admixture with the lauroyl sarcoside as indicated, it is preferred that the total amount of sarcoside be not in excess of about 5% by weight. The content of polishing material will be usually from about 20-99% by weight depending upon the specific composition such as a tooth paste or tooth powder. In general the ratio of calcium polyphosphate to hydrate aluminum oxide may be varied as desired within the range from about :1 to about 1:10 by weight, and preferably in a ratio of about 9:1. It is preferred to employ the calcium polyphosphate in an amount from about 30 to 50% by weight and the aluminum oxide hydrate in an amount from about 1 to 10% by weight in a tooth paste medium.

As indicated, the dentifrice will be in a suitable form,

In commercial practice it is preferred to use calcium pyrophosphate in view of the optimum effects such as a dental cream or tooth paste, or a tooth powder. Such composition is prepared in the usual manner. The dental creams will contain a liquid vehicle such as water, glycerine, sorbitol, propylene glycol, including suitable mixtures thereof. It is advantageous to use a mixture of both water and a humectant such as glycerine or sorbitol. It is preferred also to use a small amount of a gelling agent such as the natural and synthetic gums,

EXAMPLES I-V Dental Creams Composition Ingredient I II III IV V Sodium N-palmitoyl sareoside 2.0 1.5 1.0 1. 5 1. 5 Sodium N-lauroyl sareoside 0. 5 1. .5 .5 Calcium pyrophosphate 44. 44. 5 30.0 39. 5 44. 5 Aluminum oxide trihydrate" 5.0 5.0 200 10.0 5.0 Glycerine 22. 4 29. 4 30. 6 29. 4 29. 4 Water 16. 9 16.9 15. 4 16. 9 16. 6 Tetrasodluxn pyrophosphate 0. 25

the balance of the compositions being small amounts of gum, preservative, sweetening agent and flavor.

EXAMPLES VI-VII Tooth Powders Ingredient VI VII Sodium N-palmitoyl sarcoside 4. 0 3.0 Sodium N-lauroyl sarcoside 1. 0 Calcium pyrophosphate 84. 85 77. 75 Aluminum oxide trihydrate. 8. 5 15. 6 Flavor.- 2.5 2. 5 Soluble saccharini 15 Although the present invention has been described with reference to particular embodiments and examples, it will be apparent to those skilled in the art that variations and modifications to this invention can be made and equivalents can be substituted therefor without departing from the principles and true spirit of the invention.

Having thus described the invention, what is claimed is:

1. A dentifrice composition comprising a substantially polyphosphate and hydrated aluminum oxide in a ratio saturated aliphatic acyl amide of an amino carboxylic fron; about :1 to 1:10 by weight as a polishing materia 2. A dentifrice composition comprising a substantially saturated aliphatic acryl sarcoside compound having about 14 to 18 carbon atoms in the aliphatic acyl group, said amide having the property of substantially increasing the resistance of tooth enamel to acid attack and having less than about 15% by weight based on said amide of higher fatty acid material, the amount of said material being insuflicient to substantially adversely aflect said amide, and a mixture of about 20 to 99% by weight of a calcium polyphosphate and hydrated aluminum oxide in a ratio from about 100:1 to 1:10 by weight as a polishing material.

3. A dentifrice composition comprising palmitoyl sarco side having less than 15% by weight based on said sarcoside of higher fatty acid material, the amount of said material being insufiicient to substantially adversely affect said amide in its property of increasing the resistance of tooth enamel to acid attack, and a mixture of calcium pyrophosphate and aluminum oxide trihydrate in a ratio from about 100:1 to 1:10 by weight as a polishing material.

4. A dentifrice cornposiotion in accordance with claim 2 which contains up to 5% by weight of a mixture of palmitoyl sarcoside and lauroyl sarcoside in a ratio from about 5:1 to 1:1 by weight.

5. A dentifrice composition in the form of a dental cream in accordance with claim 3 which contains a liquid vehicle, a polishing material of calcium pyrophosphate and aluminum oxide trihyd-rate in a ratio of about 9:1 by weight, and about 2% by weight of N-higher fatty acyl sarcoside, said sarcoside being essentially sodium palmitoyl sarcoside.

6. A dental cream in accordance with claim 5 wherein said N-higher fatty acyl sarcoside is a mixture of sodium N-palmitoyl sarcoside and sodium N-lauroyl sarcoside in a ratio of about 3:1 by weight.

References Cited in the file of this patent UNITED STATES PATENTS 2,689,170 King Sept. 14, 1954 2,772,203 Salzmann Nov. 27, 1956 2,876,168 Broge et al. Mar. 3, 1959 OTHER REFERENCES Hackhs Chemical Dictionary, Julius Grant, 3rd ed., 1944, p. 158, calcium phosphate.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No, 3,033,756 May 8 19 2 Joseph Tonzetich It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.

Column 3, EXAMPLES I-V, Dental Creams second column thereof, and opposite "Glycerine", for "22.4" read 2904 column 4, line 12, for "acryl" read acyl line 32, for "composiotion" read composition Signed and sealed this 30th day of October 1962.

KSEAL) meet:

ERNEST w. SWIDER DAVID LADD Ittesting Officer Commissioner of Patents 

1. A DENTIFRICE COMPRISING A SUBSTANTIALLY SATURATAED ALIPHATIC ACYL AMIDE OF AN AMINO CARBOXYLIC ACID COMPOUND HAVING ABOUT 14 TO 18 CARBON ATOMS IN THE ALIPHATAIC ACYL GROUP, SAID AMIDE HAVING THE PROPERTY OF SUBSTANTIALLY INCREASING THE RESISTANCE OF TOOTH ENAMEL TO ACID ATTACK AND HAVING LESS THAN ABOUT 15% BY WEIGHT BASED ON SAID AMIDE OF HIGHER FATTY ACID MATERIAL, THE AMOUNT OF SAID MATERIAL BEING INSUFFICIENT TO SUBSTANTIALLY ADVERSELY AFFECT SAID AMIDE, AND A MIXTURE OF A CALCIUM POLYPHOSPHATAE AND HYDRATED ALUMINUM OXIDE IN A RATIO FROM ABOUT 100:1 TO 1:10 BY WEIGHT AS A POLISHING MATERIAL. 